. Author manuscript; available in PMC: 2016 Jun 15.

Published in final edited form as: Chem Soc Rev. 2013 Dec 4;43(5):1423–1449. doi: 10.1039/c3cs60329f

Table 1.

Candidates for cancer VOCs published during the past decade.⁴,¹⁵,⁵⁰,⁵⁶,⁶³,⁶⁸,⁷¹,⁷²,⁷⁴–⁷⁶,⁷⁸,¹³³,²⁰²,²⁴⁸,²⁴⁹ Identification of these compounds was achieved through spectral library match. A number of authors validated their identification by comparison of retention time or retention index, e.g., in ref. 1, 15, 42–45, 59, 65, 66, 131 and 133. For these VOCs the λ_b:a and λ_f:b are given in separate columns. If these partition coefficients are not known from the literature, they are estimated by regression from data in ref. 115 for hydrocarbons or estimated by the algorithms of Poulin and Krishnan¹³⁹ for other compounds based on the partition coefficients for water:air(λ_w:a) and for octanol:water (λ_o:w). All partition coefficients are given in dimensionless units [mol L⁻¹/mol L⁻¹]. Based on these physicochemical parameters, the equilibrium concentrations of VOCs in blood and fat can be estimated based on the concentration in alveolar breath

Chemical family	CAS number	Compound name	λ_b:a at 37 °C in dimensionless units [(mol L⁻¹)/(mol L⁻¹)]	References for λ_b:a at 37 °C	log[λ_fb]	References for λ_f:b at 37 °C	Tentative origin	Comments	Ref.
Alkanes, branched-chain alkanes and branched-chain alkenes	74-84-0	Ethane	8.50 × 10⁻⁰²	Predicted²⁵²	1.934	120	Natural or petrol, product of lipid peroxidation	Lung cancer	4
	109-66-0	Pentane	4.16 × 10⁻⁰¹	Measured¹¹⁵	1.998	253	Natural, possibly petrol, product of lipid peroxidation	Lung cancer	78
	142-82-5	Heptane	2.71 × 10⁺⁰⁰	Measured¹¹⁵	2.190	253	Natural or petrol, plastics	Lung cancer	78
	111-65-9	Octane	5.77 × 10⁺⁰⁰	Measured¹¹⁵	1.606	120	Natural or petrol	Lung cancer	56,78
	111-84-2	Nonane	1.39 × 10⁺⁰¹	Measured¹¹⁵	1.777	254	Natural or petrol	Breast cancer	74
	124-18-5	Decane	2.48 × 10⁺⁰¹	Predicted using data from ref. 115	1.656	254	Natural or petrol	Lung cancer	78
	1120-21-4	Undecane	5.46 × 10⁺⁰¹	Predicted using data from ref. 115	2.342		Natural or petrol	Breast cancer	76
	112-40-3	Dodecane	1.20 × 10⁺⁰²	Predicted using data from ref. 115	1.901		Fuels	Lung cancer, breast cancer	76,248
	629-50-5	Tridecane	2.67 × 10⁺⁰²	Predicted using data from ref. 115	2.540		Fuels	Breast cancer	76
	629-59-4	Tetradecane	5.99 × 10⁺⁰²	Predicted using data from ref. 115	2.990			Breast cancer	76
	629-62-9	Pentadecane	1.36 × 10⁺⁰³	Predicted using data from ref. 115	3.515			Breast cancer	76
	75-28-5	2-Methyl-propane	7.90 × 10⁻⁰²	Measured¹¹⁵	1.795		Refrigerant, contaminant from plastics, tubing, medical equipment	Breast cancer	74
	107-83-5	2-Methyl-pentane	4.73 × 10⁻⁰¹	Measured¹¹⁵	2.295	253	Petrol	Lung cancer	78
	78-79-5	Isoprene	9.50 × 10⁻⁰¹	Measured¹¹⁴	1.043	120	Mevalonic pathway – biosynthesis of cholesterol	Lung cancer and gastric cancer	15
	61141-72-8	4,6-Dimethyl-dodecane	7.38 × 10⁺⁰²	Predicted	2.178		Kerosene fuel	Head and neck cancer	63
	17302-37-3	2,2-Dimethyl-decane	1.18 × 10⁺⁰²	Predicted	1.316			Head and neck cancer	63
	473-19-8	2,2,3-Trimethyl-exobicyclo[2.2.1]heptane	1.25 × 10⁺⁰²	Predicted	2.296			Head and neck cancer	63
	562-49-2	3,3-Dimethyl-pentane	1.20 × 10⁺⁰⁰	Predicted	1.786			Breast cancer	68
	62185-53-9	5-(2-Methylpropyl)-nonane	2.86 ×10+02	Predicted	1.684			Breast cancer	68
	62238-15-7	2,3,4-Trimethyl-decane	2.99 × 10⁺⁰²	Predicted	1.755			Breast cancer	68
	589-34-4	3-Methyl-hexane	1.30 × 10⁺⁰⁰	Measured²⁵³	2.329	253	Unnatural, environmental contaminant	Head and neck cancer	63
	2213-23-2	2,4-Dimethylheptane	7.55 × 10⁺⁰⁰	Predicted	1.492		High chance of mis-assignment of isomer, petrol	Head and neck cancer, lung cancer	4,63
	3221-61-2	2-Methyl-octane	3.31 × 10⁺⁰⁰	Measured for rat blood²⁵⁴	2.040	254		Breast cancer	74
	2216-34-4	4-Methyl-octane	8.21 × 10⁺⁰⁰	Predicted	1.284		Contaminant from plastics, tubing, medical equipment	Head and neck cancer, lung cancer	4,63
	54166-32-4	2,6,6-Trimethyl-octane	4.64 × 10⁺⁰¹	Predicted	1.593			Head and neck cancer	63
	5911-04-6	3-Methyl-nonane	5.76 × 10⁺⁰⁰	Measured for rat blood²⁵⁴	2.079	254	Natural or petrol	Head and neck cancer	63
	16747-26-5	2,2,4-Trimethylhexane	7.08 × 10⁺⁰⁰	Predicted	1.426		Petrol	Lung cancer	202
	25117-31-1	5-Methyl-tridecane	7.67 × 10⁺⁰²	Predicted	2.559			Breast cancer	74
	1002-43-3	3-Methyl-undecane	1.27 × 10⁺⁰²	Predicted	1.726			Breast cancer	74
	10105-38-1	6-Methyl-pentadecane	4.86 × 10⁺⁰³	Predicted	3.689			Breast cancer	74
	6418-45-7	3-Methyl-nonadecane	2.13 × 10⁺⁰⁵	Predicted	6.830			Breast cancer	74
	6117-97-1	4-Methyl-dodecane	3.08 × 10⁺⁰²	Predicted	2.176			Breast cancer	74
	763-29-1	2-Methyl-1-pentene	1.41 × 10⁺⁰⁰	Predicted	1.783		Contaminant from plastics, tubing, medical equipment	Lung cancer	202
	2847-72-5	Decane, 4-methyl-	5.04 × 10⁺⁰¹	Predicted	2.038			Lung cancer	71
	764-13-6	2,4-Hexadiene, 2,5-dimethyl-	1.64 × 10⁺⁰⁰	Predicted	2.284			Lung cancer	71
	1515-79-3	5,5-Dimethyl-1,3-hexadiene	1.13 × 10⁺⁰⁰	Predicted	2.281			Lung cancer	72
Primary and secondary alcohols	64-17-5	Ethanol	1.50 × 10⁺⁰³	Measured²⁵²	−0.823	255	Natural, diet, disinfectants, intestinal bacterial flora	Liver cancer	50
	71-23-8	1-Propanol	1.03 × 10⁺⁰³	Measured¹²⁰	−0.532	255	Natural, disinfectants	Lung cancer	4,71
	67-63-0	2-Propanol	8.30 × 10⁺⁰²	Measured²⁵²	−0.634	255	Natural, disinfectants	Lung and breast cancer	72,75
	71-36-3	1-Butanol	9.33 × 10⁺⁰²	Measured²⁵²	−0.095	120	Natural, diet	Lung cancer	249
	104-76-7	2-Ethyl-1-hexanol	1.31 × 10⁺⁰³	Predicted	2.156		Contaminant from tubing material	Lung cancer	4
	3391-86-4	1-Octen-3-ol	1.13 × 10⁺⁰³	Predicted	2.089		Natural (produced in plants and fungi)	Liver cancer	56
	625-31-0	4-Penten-2-ol	1.39 × 10⁺⁰³	Predicted	1.006			Lung cancer	72
Aldehydes and branched aldehydes	123-38-6	Propanal	1.77 × 10⁺⁰²	Predicted	0.418		Natural or industrial waste product	Lung cancer	4
	123-72-8	Butanal	1.27 × 10⁺⁰²	Predicted	0.894		Natural or industrial waste product, diet	Lung cancer	4
	110-62-3	Pentanal	8.85 × 10⁺⁰¹	Predicted	1.361		Natural, diet	Lung cancer	4,133
	66-25-1	Hexanal	8.21 × 10⁺⁰¹	Predicted	1.769		Natural, diet	Lung cancer, liver cancer	4,56,133
	111-71-7	Heptanal	8.87 × 10⁺⁰¹	Predicted	2.058		Natural or industrial waste product, diet,	Lung cancer, breast cancer	4,75
	124-13-0	Octanal	1.26 × 10⁺⁰²	Predicted	2.209		Natural or industrial waste product diet	Lung cancer	4,133
	124-19-6	Nonanal	1.63 × 10⁺⁰²	Predicted	2.268		Possibly natural	Lung cancer	4,133
	98-01-1	Furfural\|\|furaldehyde	3.05 × 10⁺⁰³	Predicted	0.705		Natural or industrial waste product	Gastric cancer	15
Carboxylic acids	75-98-9	2,2-Dimethyl-propanoic acid	3.82 × 10⁺⁰³	Predicted	0.930			Head and neck cancer	63
Carboxylic acids	64-19-7	Acetic acid	7.96 × 10⁺⁰⁴	Predicted	−0.190		Natural or industrial waste product	Liver cancer	50
Ketones	67-64-1	Acetone	3.40 × 10⁺⁰²	Measured¹³⁷	−0.475	255	Fatty acids metabolism	Lung cancer	4
	78-93-3	2-Butanone	1.64 × 10⁺⁰²	Measured¹²⁰	−0.004	255	Diet, environmental contaminant	Lung cancer	4
	107-87-9	2-Pentanone	1.50 × 10⁺⁰²	Measured²⁵⁶	0.206	120	Natural, diet	Lung cancer	4
	591-78-6	2-Hexanone	1.68 × 10⁺⁰²	Measured¹²⁰	0.356		Industrial waste product	Lung cancer	202
	106-35-4	3-Heptanone	1.87 × 10⁺⁰²	Predicted	1.813		Natural, drugs	Lung cancer	202
	623-56-3	5-Methyl-3-hexanone	9.15 × 10⁺⁰¹	Predicted	1.702			Head and neck cancer	63
	7379-12-6	2-Methyl-3-hexanone	8.28 × 10⁺⁰¹	Predicted	1.702			Lung cancer	72
	110-93-0	6-Methyl-5-hepten-2-one	1.92 × 10⁺⁰²	Predicted	1.779		Squalene oxidation	Gastric cancer	15
	513-86-0	3-Hydroxy-2-butanone	1.02 × 10⁺⁰³	Predicted	−0.173			Lung cancer	249
	119-61-9	Benzophenone	4.14 × 10⁺⁰⁴	Predicted	2.247		Industrial waste product (used as fragrance in soaps, in pharmaceuticals and ultraviolet absorbers – sunscreen)	Lung cancer	72
	3848-24-6	2,3-Hexanedione	3.42 × 10⁺⁰⁴	Predicted	−0.189			Lung cancer	72
	565-80-0	3-Pentanone, 2,4-dimethyl-	4.27 × 10⁺⁰¹	Predicted	1.582			Lung cancer	71
Aromatic compounds	71-43-2	Benzene	8.80 × 10⁺⁰⁰	Measured²⁵⁷	1.598	257	Petrol, smoking	Lung cancer	4
	108-88-3	Toluene	1.39 × 10⁺⁰¹	Measured²⁵⁷	2.180	257	Petrol, smoking	Lung cancer	4
	100-42-5	Styrene	5.56 × 10⁺⁰¹	Measured¹²⁰	1.758	120	Natural, smoking	Lung cancer	4
	625-86-5	2,5-Dimethylfuran	2.58 × 10⁺⁰⁰	Predicted	1.695		Smoking	Lung cancer	4,71
	106-42-3	p-Xylene	3.89 × 10⁺⁰¹	Measured¹²⁰	0.709	257	Petrol, smoking	Head and neck cancer, prostate cancer	63,68
	496-16-2	2,3-Dihydro-benzofuran	8.71 × 10⁺⁰¹	Predicted	1.976			Liver cancer	50
	100-41-4	Ethylbenzene	2.82 × 10⁺⁰¹	Measured¹²⁰	1.796	120	Petrol	Lung cancer	78
	98-86-2	1-Phenyl-ethanone	1.27 × 10⁺⁰³	Predicted	1.573			Breast cancer	75
Nitrils	75-05-8	Acetonitrile	6.98 × 10⁺⁰²	Predicted	−0.198		Smoking	Lung cancer	4
	107-13-1	2-Propenenitrile	1.41 × 10⁺⁰²	Predicted	0.210		Smoking and car exhaust	Gastric cancer	15
	93946-48-6	2-Amino-5-isopropyl-8-methyl-1-azulenecarbonitrile	9.65 × 10⁺⁰⁶	Predicted	2.294			Breast cancer	68,76
Terpens and terpenoids	138-86-3	dl-Limonene	6.21 × 10⁺⁰¹	Predicted	2.296		Industrial waste (used in food flavorings and cosmetics)	Breast cancer	76
	98-55-5	p-Menth-1-en-8-ol	2.63 × 10⁺⁰³	Predicted	2.152		Cosmetics	Lung cancer	72
	21368-68-3	Camphor	2.07 × 10⁺⁰²	Predicted	1.873		Natural	Lung cancer	72
Others	110-27-0	Isopropyl myristate	5.75 × 10⁺⁰⁴	Predicted	2.298			Breast cancer	75
	124-63-0	Methane-sulfonyl chloride	2.65 × 10⁺⁰²	Predicted	0.021		Transamination pathways (incomplete metabolism of methionine)	Liver cancer	50
	631-61-8	Ammonium acetate						Head and neck	63
	35242-43-4	2,3-Dihydro-1-phenyl-4(1H)-quinazolinone	3.84 × 10⁺⁰⁷	Predicted	2.260			Breast cancer	68,75
	4282-42-2	1-Iodo-nonane	3.72 × 10⁺⁰²	Predicted	2.298			Breast cancer	68
	24310-22-3	2-[(1,1-Dimethylethyl)thio]-acetic acid	9.66 × 10⁺⁰⁵	Predicted	1.767			Colon cancer	68
	82406-83-5	4-(4-Propylcyclohexyl)-, 4′-cyano[1,1′-biphenyl]-4-yl ester benzoic acid	1.77 × 10⁺¹¹	Predicted	2.298			Colon cancer	68
	NIST 282650	2-Trifluoromethylbenzoic acid, 6-ethyl-3-octyl ester	1.18 × 10⁺⁰⁵	Predicted	2.298			Breast cancer	68
	21064-19-7	1,5,9-Cyclododecatriene, 1,5,9-trimethyl-	1.05 × 10⁺⁰³	Predicted	2.298			Lung cancer	71
	6846-50-0	Pentan-1,3-dioldiisobutyrate, 2,2,4-trimethyl	8.50 × 10⁺⁰⁴	Predicted	2.293		Plasticizer	Lung cancer	71
	23676-09-7	Benzoic acid, 4-ethoxy-, ethyl ester	2.07 × 10⁺⁰⁴	Predicted	2.266			Lung cancer	71
	74381-40-1	Propanoic acid, 2-methyl-, 1-(1,1-dimethylethyl)-2-methyl-1,3-propanediyl ester	7.68 × 10⁺⁰⁴	Predicted	2.293			Lung cancer	71
	494-19-9	10,11-Dihydro-5H-dibenz-[b,f]-azepine	5.37 × 10⁺⁰⁵	Predicted	2.286			Lung cancer	71
	719-22-2	2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-	1.69 × 10⁺⁰⁷	Predicted	2.283			Lung cancer	71
	101-84-8	Benzene, 1,1-oxybis-	2.43 × 10⁺⁰³	Predicted	2.292			Lung cancer	71
	13049-35-9	1,1-Biphenyl, 2,2-diethyl-	6.68 × 10⁺⁰⁴	Predicted	2.298			Lung cancer	71
	87-44-5	trans-Caryophyllene	1.81 × 10⁺⁰²	Predicted	2.298			Lung cancer	71
	3910-35-8	1H-Indene, 2,3-dihydro-1,1,3-trimethyl-3-phenyl-	3.22 × 10⁺⁰⁴	Predicted	2.298			Lung cancer	71
	84-66-2	1,2-Benzenedicarboxylic acid, diethyl ester	3.85 × 10⁺⁰⁴	Predicted	2.154		Plasticizer	Lung cancer	71
	76-13-1	Ethane, 1,1,2-trichloro-1,2,2-trifluoro-	2.40 × 10⁻⁰¹	Predicted	2.245			Lung cancer	72
	1634-04-4	Propane, 2-methoxy-2-methyl-	1.59 × 10⁺⁰¹	Predicted	0.728	258	Gasoline	Lung cancer	72
	42848-06-6	1-Propene, 1-(methylthio)-, (E)-	8.18 × 10⁺⁰⁰	Predicted	2.043		Diet (onion, garlic)	Lung cancer	72
	824-22-6	1H-Indene, 2,3-dihydro-4-methyl-	1.32 × 10⁺⁰²	Predicted	2.280			Lung cancer	72
	915392-37-9	5-Isopropenyl-2-methyl-7-oxabicyclo[4.1.0]heptan-2-ol	5.97 × 10⁺⁰⁵	Predicted	1.473			Lung cancer	72
	127-51-5	Isomethyl ionone	1.95 × 10⁺⁰³	Predicted	2.291			Lung cancer	72
	710336-76-8	2,2,7,7-Tetramethyltricyclo-[6.2.1.0(1,6)]undec-4-en-3-one	4.33 × 10⁺⁰²	Predicted	2.274			Lung cancer	72
	24238-73-1	Bicyclo[3.2.2]nonane-1,5-dicarboxylic acid, 5-ethyl ester	3.20 × 10⁺⁰⁶	Predicted	1.868			Lung cancer	72
	959016-51-4	Pentanoic acid, 2,2,4-trimethyl-3-carboxyisopropyl, isobutyl ester	1.27 × 10⁺⁰⁴	Predicted	2.295			Lung cancer	72
	16204-36-7	1,2,4,5-Tetroxane, 3,3,6,6-tetraphenyl-	9.14 × 10⁺⁰⁸	Predicted	2.295			Lung cancer	72
	6738-27-8	2,5-Cyclohexadien-1-one, 2,6-bis(1,1-dimethylethyl)-4-ethylidene-	3.38 × 10⁺⁰³	Predicted	2.292			Lung cancer	72
	55162-49-7	Furan, 2-[(2-ethoxy-3,4-dimethyl-2-cyclohexen-1-ylidene)methyl]-	3.47 ’ 10⁺⁰³	Predicted	2.297			Lung cancer	72
	7694-30-6	Benzene, 1,1-(1,2-cyclobutanediyl)bis, cis-	2.85 × 10⁺⁰⁴	Predicted	2.296			Lung cancer	72
	53699-80-2	Benzene, 1,1-[1-(ethylthio)propylidene]bis-	1.09 × 10⁺⁰⁵	Predicted	2.295			Lung cancer	72
	101580-33-0	Anthracene, 1,2,3,4-tetrahydro-9-propyl-	2.45 × 10⁺⁰⁵	Predicted	2.298			Lung cancer	72
	839-73-6	9,10-Anthracenediol, 2-ethyl-	2.79 × 10⁺¹¹	Predicted	2.284			Lung cancer	72
	10224-91-6	Benzene, 1,1-ethylidenebis, 4-ethyl-	6.30 × 10⁺⁰⁴	Predicted	2.298			Lung cancer	72